We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Orphan Annie's Schoolhouse Inn

8097 School St., Baileys Harbor, WI
Orphan Annie's Schoolhouse Inn
Write a Review

18 reviews from our community

Rate and write a review
Roll over, then click to rate
  Click to rate
Traveler rating
    11
    1
    1
    3
    2
See reviews for
1
11
Solo
0
Business
0
Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room Tips
Date | Rating
  • English first
  • Any
English first
  • All months
    (18)
  • Mar-May only
    (0)
  • Jun-Aug only
    (11)
  • Sep-Nov only
    (7)
  • Dec-Feb only
    (0)
All months
Chicago, Illinois
Level Contributor
6 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed September 5, 2014

I really enjoyed my stay here. It is a converted schoolhouse which has 5 suites; we stayed in the Light House suite. Loren and Annie were very welcoming and great hosts. Check in was smooth; I was on a bike and they let me park it in the shed. The room itself was spacious, clean and quiet. It's basically one... More 

Was this review helpful? Yes 2
kiel
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed August 6, 2014

This place was wonderful. Loren and Annie did a great job decorating, and were very friendly. They genuinely cared about if we were having a good time. Upon arrival they gave us quite a bit of reading material that highlighted the attractions of the area. They were very approachable the entire time. We will be staying here again; perhaps next... More 

Was this review helpful? Yes 1
Halstead, Kansas
Level Contributor
212 reviews
29 hotel reviews
common_n_hotel_reviews_1bd8 63 helpful votes
5 of 5 stars Reviewed August 4, 2013 via mobile

We have stayed here every summer, for about the past 15 years, and wouldn't go anywhere else. The rooms are large, impeccably clean and have nice decks. And, yes, Loren and Annie have rules, but that's one reason we stay there. It's just very nice and quiet, and you won't find nicer rooms and better value.

Was this review helpful? Yes 4
Pewaukee, Wisconsin
Level Contributor
8 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed October 8, 2012

I could not have been more pleased with our stay at this inn! From contacting Loren about the room and details to the incredibly clean rooms and grounds. Loren and his wife were very very nice and happy to help you in any way. A lot of charm to this old school house turned inn. Yes the floors are squeaky,... More 

Was this review helpful? Yes 1
Milwaukee, Wisconsin
Level Contributor
18 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed October 7, 2012

I just arrived home from my first stay here. I was slightly hesitant upon my arrival after reading the reviews. I will say that as a WEEKLY business traveler for 5 years I have never seen a cleaner room! We stayed in the Homestead Suite. It was super quiet at night. Baileys Harbor is on the quieter side of the... More 

Was this review helpful? Yes 1
Mokena, Illinois
Level Contributor
18 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
3 of 5 stars Reviewed September 5, 2012

Only complaints were the horribly squeaky floors and the worn out bed. You roll to the middle of the bed. Also the bed is advertised as "Queen size". It is a full size bed, not a queen size. The room (Upper Deck) was nicely decorated and comfortably furnished. We weren't given any "rules" and the owners seemed fine. One telling... More 

Was this review helpful? Yes
Milwaukee, Wisconsin
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
1 of 5 stars Reviewed July 21, 2012

We found Orphan Annie's at Bailey's Harbor and wanted to reserve for mid July 2013 for a dance festival in Door County. We talked to the innkeepers on Sunday, July 15, 2012 and reserved a room and wrote a check for 1/2 of the amount. We were given the "rules" of no more that 2 guests for only 1 hour... More 

Was this review helpful? Yes 2
Chicago
Level Contributor
129 reviews
43 hotel reviews
common_n_hotel_reviews_1bd8 121 helpful votes
5 of 5 stars Reviewed July 14, 2012

If you don't need a lake view, this is a lovely place to stay. It's one block out of the center of town, so you can walk to the lake in minutes. The old converted school house is on a park and very quiet. The rooms are large and comforable, each with porches. They don't serve breakfast, but they have... More 

Was this review helpful? Yes 1
Madison, Wisconsin
1 review
common_n_hotel_reviews_1bd8 5 helpful votes
1 of 5 stars Reviewed July 10, 2012

My warning system went on alert immediately as there were notes with rules pasted all over the room, including cleaning the shower stall every day. Some friends of ours live in the area and wanted to see the room. Oh my lord, you think we were having a bachelor party the way Loren reacted. We were lectured and scolded as... More 

Was this review helpful? Yes 5
Fairfield Glade, Tennessee
Level Contributor
63 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 16 helpful votes
5 of 5 stars Reviewed November 18, 2011

We recently stayed here for the second time, and confirmed that it's indeed a wonderful choice. A very unique place, my wife and I stayed in the Library room (was actually the library when the building was a school) which is more like a suite. It has a small kitchen area, walk-in closet and lots of space. It's decorated with... More 

Was this review helpful? Yes 1
Questions? Get answers from hotel staff and past guests. Ask a question

8 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (4)
Viewed
Room/suite (1)
Viewed
Hotel & grounds (2)
Viewed
Other (1)

Management photos: Courtesy of the property manager

Viewed
All management photos (4)
Viewed
Other (4)
Check In Check Out
Show Prices
Hotels you might also like...
Also consider these accommodations in or near Baileys Harbor
6.9 mi away
Edgewater Resort
Edgewater Resort
#4 of 8 in Ephraim
4.5 of 5 stars 396 reviews
8.7 mi away
Country House Resort
Country House Resort
#4 of 17 in Sister Bay
4.5 of 5 stars 285 reviews
1.5 mi away
Maxwelton Braes Lodge
Maxwelton Braes Lodge
#4 of 7 in Baileys Harbor
4.0 of 5 stars 16 reviews
Show Prices
Show Prices
Show Prices
7.5 mi away
The Ashbrooke
The Ashbrooke
#1 of 7 in Egg Harbor
4.5 of 5 stars 213 reviews
6.8 mi away
Homestead Suites
Homestead Suites
#3 of 10 in Fish Creek
4.5 of 5 stars 152 reviews
18.0 mi away
Westwood Shores Waterfront Resort
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities